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Preparation of Quinazolines via a 2+2+2 Annulation from Aryldiazonium Salts and Nitriles

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journal contribution
posted on 12.07.2017, 00:00 by Mani Ramanathan, Shiuh-Tzung Liu
A (2+2+2) modular synthesis of multisubstituted quinazolines has been realized by the direct reaction of aryldiazonium salts with two equivalent of nitriles. Reaction of aryldiazonium salt with a nitrile provides the initial formation of a reactive nitrilium ion, which is attacked by another molecule of nitrile followed by electrophilic cyclization to deliver the desired product. Notable flexibility in the substitution patterns, readily available substrates, short reaction time, transition metal-free, and gram-scale synthesis are the advantages of this method.